I don’t think it’s an adapter issue. It makes no difference to my issues whether I am using the USB-A on the back of the iMac or the USB-A of an Intel certified Thunderbolt 3 dock.
Currently I have no problems routing one iLok through to a Windows 10 VM in Catalina, but as soon as I plug in a second iLok I cannot run one in Windows and one in Catalina at the same time. It causes various lock-ups, missing dongles or even dongles missing licenses. I tried with a mix of using the dock + machine ports, machine + machine ports, dock + dock ports, USB hubs, etc.
It is all fine in Mojave. USB sharing in Parallels Catalina is struggling though. Anybody tried VMWare Fusion?